Sodium Hydroxide → HCID 86718238, compound

HRID 2401648Notes

Reaction equation

HRID 2401648 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10]C)=[O:9].[CH:12]1([CH2:18][O:19][C:20]2[C:21]3[N:22]([C:26]([C:30](O)=[O:31])=[C:27]([CH3:29])[N:28]=3)[CH:23]=[CH:24][CH:25]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.F[B-](F)(F)F.N1(O[C+](N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[OH-].[Na+]>CS(C)=O>[CH:12]1([CH2:18][O:19][C:20]2[C:21]3[N:22]([C:26]([C:30]([NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:31])=[C:27]([CH3:29])[N:28]=3)[CH:23]=[CH:24][CH:25]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 11499324Methyl 6-aminohexanoate hydrochlorideHCID 711084908-(Cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 178484679HCID 178484679, compound

Product 1

HCID 86718238HCID 86718238, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

18 mg of methyl 6-aminohexanoate hydrochloride (0.1 mmol, 1.0 equivalent) were initially charged, and 29 mg of 8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid Example 6A (0.1 mmol, 1 equivalent) in 0.3 ml of DMSO, 41.7 mg of (benzotriazol-1-yloxy)bisdimethylaminomethyliumfluoroborate (TBTU, 0.13 mmol, 1.3 equivalents) in 0.3 ml of DMSO and 26 mg of N,N-diisopropylethylamine (0.2 mmol, 2 equivalents) were added in succession. The mixture was shaken at RT overnight, 0.4 ml of 2 N sodium hydroxide solution was added and the mixture was once more shaken at RT overnight. The solvent was then evaporated and the mixture was purified by preparative HPLC (Method 10). This gave 11 mg (26% of theory; purity: 100%) of the title compound.

Workup

  1. stirringthe mixture was once more shaken at RT overnight
  2. customThe solvent was then evaporated
  3. customthe mixture was purified by preparative HPLC (Method 10)

Sources & evidence

ORD record
ord-7cf2d8cdd5a34822946ee35b8b475e11
Source dataset
uspto-grants-2014_08
Patent number
US08796305B2

Reaction notes

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